Failing at Failure

Recently I was asked to speak to a group of Macalester sophomores about the lessons one learns from failure. Since this was the second time I was asked to address this particular topic, I must assume that I am perceived as something of an expert—sort of the go-to guy on failing.

Problem is, I’m a bad example and therefore, on this subject, probably a bad teacher. The “failure” part I’ve pretty much mastered; it’s the “learning from” part with which I continue to struggle. About the only quality I might share with Michael Jordan is an aversion to failure that borders on the pathological—and I am burdened by a lower shooting percentage.

I did try looking up inspirational quotations, in the hope that others had discovered a degree of acceptance and general peppiness that has thus far eluded me. When I came across, in several sources, a quotation from James Joyce—“Mistakes are the portals of discovery”’—I was delighted if a bit surprised, since Joyce is one of my favorite authors but not one I associate with a hearty pat on the back. Turns out I was right to be surprised, since the actual quotation from Joyce’s Ulysses—“Bosh! Stephen said rudely. A man of genius makes no mistakes. His errors are volitional and are the portals of discovery”—is spoken by the highly unreliable and generally immature Stephen Dedalus and is more about arrogance than acceptance. For what it’s worth, the quotations attributed at BrainyQuote.com to Donald Trump and Coco Chanel appear to be more accurately reported.

Suggesting to students that failure is commonly uplifting feels to me deeply false, as does suggesting that most failure is part of a long journey toward deeper understanding. Sometimes failure is a precursor to great discovery, but sometimes failure is just failure, and more often than not there is nothing uplifting about it. And yet it is a part of every life, something with which all of us must learn to cope and from which all of us must learn to recover.

The important lesson to teach, in my view, is not as much about the benefits of failure as about the necessity of resilience, and this may be a lesson we actually obscure by minimizing the extent to which failure can be painful and pointless. In other words, if all failure is understood as serving a larger purpose—if it is just another step on the stairway to success—it should not be deeply difficult to handle. But it is difficult. It does not always fit neatly into a personal moral fable. Overcoming it takes effort of a kind that should never be minimized.

Here, I think, is where we do not do an especially good job at Macalester or at most colleges—and more broadly as a generation of parents—at educating our students or our children. We are so focused on assuring them that everything will be all right that we leave them ill prepared for those moments when everything is not. Sometimes they will not achieve their goals; sometimes they will not measure up; sometimes they will be rejected. Then what?

The interesting question for colleges is how best to build resilience in students without subjecting them to the needlessly painful, or to things, like poor grades, that could have lasting, negative consequences for their lives. In environments that so prioritize safety, support, and success, can we teach students what it feels like to be (metaphorically, of course) knocked down? If we take our jobs as educators seriously, this is a question with which we should wrestle.

Here is one suggestion: create as part of the educational experience situations in which students are incentivized to succeed but likely to fail. Make the failure, and the reasons for failure, clear, but the consequences minor. Think of this as failure with a net: the tumble is real and unpleasant but does no lasting damage. Getting back on the tightrope becomes just a little bit scarier—and that is the point.

Such situations can be created in classrooms, laboratories, and studios, and I’m betting that they sometimes are. (I had several such experiences in chemistry laboratories, though these appear to have been unplanned.) But since there is, always, that tricky detail of grades, experiences outside traditional academic settings merit thoughtful consideration.

One reason why the growing interest in entrepreneurship at Macalester intrigues me is that it seems like a wonderful opportunity to provide students with real but not deeply consequential experiences with failure. Even the most successful entrepreneurs tend to have an intimate familiarity with failure. Student entrepreneurs in particular can build successful businesses or alleviate social problems, but the odds are small that they will do so on a first or second or third try. Mostly, driven by great passion and intelligence, they will try, and they will not succeed, and that will be an invaluable part of their education in the nature of life.